RT Journal Article
SR Electronic
T1 Metabolism of sodium nifurstyrenate, a veterinary antimicrobial nitrofuran, in animals and fish.
JF Drug Metabolism and Disposition
JO Drug Metab Dispos
FD American Society for Pharmacology and Experimental Therapeutics
SP 226
OP 233
VO 20
IS 2
A1 K Tatsumi
A1 S Kitamura
A1 M Kato
A1 K Hiraoka
YR 1992
UL http://dmd.aspetjournals.org/content/20/2/226.abstract
AB Sodium nifursyrenate [beta-(5-nitro-2-furyl)-p-carboxystyrene sodium salt, NSA-Na] is an antibacterial nitrofuran which has been widely used for prevention and treatment of bacterial infections in fish in Japan. When NSA-Na was anaerobically incubated with rabbit liver cytosol and 2-hydroxypyrimidine, 1-(p-carboxyphenyl)-5-cyano-3-oxo-1,4-pentadiene (cyano-pentadienone), 1-(p-carboxyphenyl)-5-cyano-3-oxo-1-pentanone (cyano-pentanone), and 1-(p-carboxyphenyl)-5-cyano-3-pentanone (cyano-pentanone) were isolated and identified as the metabolites of the nitrofuran. In addition, when cyano-pentenone and cyano-pentanone were aerobically incubated with the liver preparation and NADPH, 1-(p-carboxyphenyl)-5-cyano-3-hydroxy-1-pentene (cyano-pentenol) and 1-(p-carboxyphenyl)-5-cyano-3-pentanol (cyano-pentanol) were also isolated and identified as the metabolites of the nitrofuran in its further metabolism, respectively. The anaerobic incubation of NSA-Na with rat liver cytosol and 2-hydroxypyrimidine resulted in the formation of cyano-pentadienone and cyano-pentanone. In this case, however, cyano-pentenone was not detectable. On the other hand, when NSA-Na was anaerobically incubated with sea bream liver cytosol and NADPH, the formation of cyano-pentenone, cyano-pentanone, and cyanopentenol, but not cyano-pentadienone, was observed. Furthermore, cyano-pentanone was metabolized to cyano-pentanol by the fish liver preparation with NADPH under aerobic conditions. When NSA-Na was given orally to rabbits, cyano-pentanone, cyano-pentenol, cyano-pentanol, and beta-(acetamido-2-furyl)-p-carboxystyrene (acetamidofuran) were identified as the urinary metabolites of the nitrofuran.(ABSTRACT TRUNCATED AT 250 WORDS)